4-Chlorobenzonitrile → 4-Chlorobenzenehydroxamic acid

HRID 538553

Reaction equation

HRID 538553 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#N)=[CH:4][CH:3]=1.[ClH:10].[NH2:11][OH:12].[OH-:13].[Na+]>CCO>[Cl:10][C:2]1[CH:9]=[CH:8][C:5]([C:6]([NH:11][OH:12])=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 121634-ChlorobenzonitrileHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 5871784-Chlorobenzenehydroxamic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-chlorobenzonitrile (10.0 g, 73.0 mmol) in EtOH (250 mL) was added hydroxylamine hydrochloride (5.03 g, 73.0 mmol) and NaOH (2.90 g, 73.0 mmol). The resulting reaction mixture was refluxed for 15 h. After the completion of the reaction (TLC monitoring), the mixture was concentrated, added EtOH and filtered. The filtrate was evaporated in vacuo and used as such for the next step (crude yield 12.0 g, 66%).

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 15 h
  3. customAfter the completion of the reaction (TLC monitoring)
  4. concentrationthe mixture was concentrated
  5. additionadded EtOH
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-cf0717949109400cad0d352f03afe04d
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Linked notes

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